ABSTRACT
Fifteen alkaloid compounds were isolated from the 70% aqueous alcohol extract of Stephania tetrandra S. Moore by silica gel, reversed phase silica gel, Sephadex LH-20 column chromatography and semi-preparative high performance liquid chromatography. They were identified as tetrandraside A (1), (Z)-N-formyl-nornuciferin (2), (E)-N-formyl-nornuciferin (3), salutaridine (4), salutaridine N-oxide (5), (E)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-2 propenamide (6), dauriporphine (7), sinomenine (8), liriodenine (9), α-magnoflorine (10), (1S)-4'-β-glucosylcoclaurine (11), tetrandrine (12), fangchinoline (13), tetrandrine 2'-β-oxide (14), and tetrandrine 2'-α-oxide (15), respectively, by MS, NMR and single crystal diffraction. Among them, compound 1 is a new alkaloid glycoside. Compounds 2-11 were obtained from this plant for the first time. These compounds showed obvious cytotoxic activity against drug-resistant lung cancer cell line H1299, and compound 9 had the best activity, with an IC50 of 5.38 μmol·L-1.
ABSTRACT
Silica gel, Sephadex LH-20, and reverse phase (C-18) column chromatography were used for the research of chemical constituents occurred in Arisaema flavum(Forsk.) Schott. The structures were elucidated by comparison physico-chemical properties and NMR spectroscopic data with those of known compounds. Seventeen cerebrosides were identified as 1-O-β-D-glucopyranosyl-(2S, 3R, 4E, 8E)-2-[(2'(R)-acetoxyoctadecanoyl)amido]-4, 8-octadecadiene-1, 3-diol (1), 2'-O-acetylsoyacerebroside I (2), 1-O-(β-D-glucopyranosyl)-(2S, 3R, 4E, 13Z)-2-[(2'R)-2-hydroxytetradecanoylamino]-1, 3-dihydroxy-4, 13-docosadiene (3), (2S, 3R, 4E, 8E)1-(β-D-glucopyranosyl)-3-hydroxy-2-[(R)-2'-hydroxyhexadecanoyl]amino-9-methyl-4, 8-heptadecadiene (4), (2S, 3R, 4E, 8E)1-(β-D-glucopyranosyl)-3-hydroxy-2-[(R)-2'-hydroxyhexadecanoyl]amino-9-methyl-4, 8-octadecadiene (5), (2S, 3R, 4E, 8E)1-(β-D-glucopyranosyl)-3-hydroxy-2-[(R)-2'-hydroxypalmitoyl]amino-9-methyl-4, 8-octadecadiene (6), (2S, 3R, 4E, 8E)1-(β-D-glucopyranosyl)-3-hydroxy-2-[(R)-2'-hydroxyoctadecanoyl]amino-9-methyl-4, 8-octadecadiene (7), 1-O-(β-D-glucopyranosyl)-(2S, 3R, 4E, 8E)-2-[(R)-2'-hydroxytetradecanoylamino]-4, 8-octadecadiene-1, 3-diol (8), 1-O-(β-D-glucopyranosyl)-(2S, 3R, 4E, 8E)-2-[(R)-2'-hydroxypentadecanoylamino]-4, 8-octadecadiene-1, 3-diol (9), 1-O-(β-D-glucopyranosyl)-(2S, 3R, 4E, 8E)-2-[(R)-2'-hydroxyhexadecanoylamino]-4, 8-octadecadiene-1, 3-diol (10), 1-O-(β-D-glucopyranosyl)-(2S, 3R, 4E, 8Z)-2-[(R)-2'-hydroxyhexadecanoylamino]-4, 8-octadecadiene-1, 3-diol (11), 1-O-(β-D-glucopyranosyl)-(2S, 3R, 4E, 8E)-2-[(R)-2'-hydroxyoctadecanoylamino]-1, 3-hydroxy-4, 8-octadecadiene (12), 1-O-(β-D-glucopyranosyl)-(2S, 3R, 4E)-2-[(R)-2'-hydroxytetracosanoylamino]-1, 3-hydroxy-4-hexadecane (13), 1-O-(β-D-glucopyranosyl)-(2S, 3R, 4R, 8Z)-2N-[(2'R)-2'-hydroxytetracosanoyl]-8-(Z)-octadecene-1, 3, 4-triol (14), 1-O-(β-D-glucopyranosyl)-(2S, 3S, 4E, 8E)-2N-[(2'R)-2'-hydroxyhexadecanoyl]-4-(E), 8-(Z)-octadecadiene-1, 3-diol (15), typhoniside A (16), and 1-O-β-D-glucopyranosyl-(2S, 3R, 8E)-2-[(2'R)-2-hydroxypalmitoylamino]-8-octadecene-1, 3-diol (17). Compounds 1 and 2 were isolated from the plant for the first time, while the remained compounds were isolated from the genus Arisaema for the first time.
ABSTRACT
To study the chemical constituents of Clematoclethra scandens subsp. actinidioides, chromatographic methods such as silica gel and MCI column chromatographic technology, and preparative HPLC were used and sixteen compounds were isolated from the aerial parts of this plant. By using spectroscopic techniques including 1H, 13C-NMR, HMBC and ESI-MS, these compounds were identified as betulinic acid (1), ursolic acid (2), oleanic acid (3), corosolic acid (4), 3beta-(trans-p-coumaroyloxy)-2alpha, 23-dihydroxyurs-12-en-28-oic acid (5), 3beta-(trans-p-coumaroyloxy)-2alpha, 23-dihydroxyurs-12, 20 (30)-dien-28-oic acid (6), 2alpha, 3alpha, 23-trihydroxyurs-12, 20 (30)-dien-28-oic acid (7), 2alpha, 3alpha, 23-trihydroxyurs-12-en-28-oic acid (8), asiatic acid (9), 2alpha, 3alpha, 24-tri-hydroxyurs-12-en-28-oic acid (10), 2alpha, 3beta, 23-trihydroxyurs-12, 20 (30)-dien-28-oic acid (11), 2alpha, 3beta, 19alpha, 24-tetrahydroxyurs-12-en-28-oic acid (12), 2alpha, 3alpha, 19alpha, 24-tetrahydroxyurs-12-en-28-oic acid (13), 2alpha, 3beta, 23, 24-tetrahydroxyurs-12-en-28-oic acid (14), 2alpha, 3alpha, 19alpha, 23, 24-pentahydroxyurs-12-en-28-oic acid (15) and daucosterol (16). Among them, compounds 3-6, 11-12, 14 and 15 were isolated from this endemic plant for the first time.